
Chicago’s fall foliage transforms the city of work into a city of magic. It is as dynamic as it is enchanting. Autumn in the Windy City doesn’t just mean the changing colors of leaves. It also means the vibrant, festive events that paint the city in hues of excitement and joy.
What makes Chicago’s Fall so special?
Chicago’s fall is a riot of color and flavor. From the crisp air off Lake Michigan to the inviting aromas of seasonal brews. The city’s heart is beating to the rhythm of a variety of festive activities that caters to all tastes. These 10 experiences will make you fall in love with Chicago again, whether you’re a resident or a tourist.
1. Architecture River Cruise
Take a trip through the rich architectural history of the city. You’ll learn the stories behind Chicago’s skyline as the cool breeze from the river brushes your face.
2. Bobby’s Bike Ride
Take in the sights and sounds as you pedal through the streets of Chicago. This is the perfect family adventure that will leave you with unforgettable memories.

3. Bengtson’s Pumpkin Farm
Enjoy Halloween without the horrors. Bengtson’s offers a cozy family-friendly environment with a petting farm, pumpkins galore, and pig races.
4. Konow’s Corn Maze
Get lost in a labyrinth made of tall cornstalks against the autumn sky. The maze is only the beginning of the adventure. The real fun lies in the activities that await you at every turn.
5. Sonny Acres Farm
Let your imagination run wild as you choose the perfect pumpkin. Sonny Acres Farm will be the setting for your fall fantasies. Enjoy wagon rides, a spinning tunnel and more.
6. Night of 1,000 Jack-o-Lanterns
Prepare to be dazzled as you gaze at a thousand pumpkins. Each one is a work of art. The Chicago Botanic Garden is transformed into a Halloween paradise that is both educational and enchanting.
7. Naperville Oktoberfest
Naperville’s Oktoberfest will soon be here. Toast the season with steins filled with fine German beer and dance to lively oompah songs that fill the air.

8. Lincoln Avenue Apple Fest
Enjoy the tart sweetness of apple desserts as you stroll along the streets. Apple Fest is a sweet-tooth’s dream, with pies and ciders, carnival rides, and other delights.
9. Chicago International Film Festival
The Chicago International Film Festival, a must-attend event for cinephiles. The festival’s lineup showcases the best in global cinema. It is an experience that takes you to the heart and soul of storytelling.
10. The Realm of Terror Haunted House
Step into the Realm of Terror if you dare. This haunted house takes fear to an entirely new level. It offers a thrilling experience sure to get your heart pumping.
The City that Has it All
Chicago in the embrace of autumn is a city with something for everyone. It’s a city where you can create lasting memories. In Chicago, each fall is a brand new chapter in your life’s book, and you won’t want it to slip by.